Synthetic analogues (indolactams) of (-)-indolactam-V are new congeners of the teleocidin class of tumor promoters

Mitsuru Hirota, Masami Suganuma, Shigeru Yoshizawa, Takahiko Horiuchi, Michie Nakayasu, Masashi Hasegawa, Yasuyuki Endo, Koichi Shudo, Hirota Fujiki

研究成果: ジャーナルへの寄稿記事

19 引用 (Scopus)

抄録

(-)-Indolactam-V, which has the partial structure of teleocidins A and B, and has tumor-promoting activity, is a good model for use in studies on the relation between structure and tumor-promoting activity, whereas (+)-indolactam-V has no tumor-promoting activity. In this work, five racemic indolactams differing only in their alkyl group at C-12 of (-)-indolactam-V were synthesized and tested for biological and biochemical activities related to tumor promotion. The activities tested were inductions of ornithine decarboxylase in mouse skin and human promyelocytic leukemia (HL-60) cell adhesion, inhibition of specific [3H]12-O-tetradecanoyl-phorbol-13-acetate binding to a mouse particulate fraction and activation of protein kinase C in vitro. The results showed that (±)-indolactam-L and (±)-indolactam-F had almost the same activities as (±)-indolactam-V, suggesting that (-)-indolactam-L and (-)-indolactam-F are new tumor promoters with as high potency as (-)-indolactam-V. (±)-Indolactam-t-L, which has a highly lipophilic group at C-12 of (-)-indolactam-V, showed the highest activities in the above tests. (-)-Indolactam-t-L might have stronger tumor-promoting activity than (-)-indolactam-V. Furthermore, the results with (-)-indolactam-t-L indicated the possibility of designing new tumor promoters with stronger activity than teleocidin.

元の言語英語
ページ(範囲)577-582
ページ数6
ジャーナルJapanese Journal of Cancer Research
78
発行部数6
出版物ステータス出版済み - 6 1 1987
外部発表Yes

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Carcinogens
Neoplasms
Ornithine Decarboxylase
HL-60 Cells
Tetradecanoylphorbol Acetate
indolactam V
teleocidins
Cell Adhesion
Protein Kinase C
Leukemia
Skin

All Science Journal Classification (ASJC) codes

  • Oncology
  • Cancer Research

これを引用

Hirota, M., Suganuma, M., Yoshizawa, S., Horiuchi, T., Nakayasu, M., Hasegawa, M., ... Fujiki, H. (1987). Synthetic analogues (indolactams) of (-)-indolactam-V are new congeners of the teleocidin class of tumor promoters. Japanese Journal of Cancer Research, 78(6), 577-582.

Synthetic analogues (indolactams) of (-)-indolactam-V are new congeners of the teleocidin class of tumor promoters. / Hirota, Mitsuru; Suganuma, Masami; Yoshizawa, Shigeru; Horiuchi, Takahiko; Nakayasu, Michie; Hasegawa, Masashi; Endo, Yasuyuki; Shudo, Koichi; Fujiki, Hirota.

:: Japanese Journal of Cancer Research, 巻 78, 番号 6, 01.06.1987, p. 577-582.

研究成果: ジャーナルへの寄稿記事

Hirota, M, Suganuma, M, Yoshizawa, S, Horiuchi, T, Nakayasu, M, Hasegawa, M, Endo, Y, Shudo, K & Fujiki, H 1987, 'Synthetic analogues (indolactams) of (-)-indolactam-V are new congeners of the teleocidin class of tumor promoters', Japanese Journal of Cancer Research, 巻. 78, 番号 6, pp. 577-582.
Hirota, Mitsuru ; Suganuma, Masami ; Yoshizawa, Shigeru ; Horiuchi, Takahiko ; Nakayasu, Michie ; Hasegawa, Masashi ; Endo, Yasuyuki ; Shudo, Koichi ; Fujiki, Hirota. / Synthetic analogues (indolactams) of (-)-indolactam-V are new congeners of the teleocidin class of tumor promoters. :: Japanese Journal of Cancer Research. 1987 ; 巻 78, 番号 6. pp. 577-582.
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title = "Synthetic analogues (indolactams) of (-)-indolactam-V are new congeners of the teleocidin class of tumor promoters",
abstract = "(-)-Indolactam-V, which has the partial structure of teleocidins A and B, and has tumor-promoting activity, is a good model for use in studies on the relation between structure and tumor-promoting activity, whereas (+)-indolactam-V has no tumor-promoting activity. In this work, five racemic indolactams differing only in their alkyl group at C-12 of (-)-indolactam-V were synthesized and tested for biological and biochemical activities related to tumor promotion. The activities tested were inductions of ornithine decarboxylase in mouse skin and human promyelocytic leukemia (HL-60) cell adhesion, inhibition of specific [3H]12-O-tetradecanoyl-phorbol-13-acetate binding to a mouse particulate fraction and activation of protein kinase C in vitro. The results showed that (±)-indolactam-L and (±)-indolactam-F had almost the same activities as (±)-indolactam-V, suggesting that (-)-indolactam-L and (-)-indolactam-F are new tumor promoters with as high potency as (-)-indolactam-V. (±)-Indolactam-t-L, which has a highly lipophilic group at C-12 of (-)-indolactam-V, showed the highest activities in the above tests. (-)-Indolactam-t-L might have stronger tumor-promoting activity than (-)-indolactam-V. Furthermore, the results with (-)-indolactam-t-L indicated the possibility of designing new tumor promoters with stronger activity than teleocidin.",
author = "Mitsuru Hirota and Masami Suganuma and Shigeru Yoshizawa and Takahiko Horiuchi and Michie Nakayasu and Masashi Hasegawa and Yasuyuki Endo and Koichi Shudo and Hirota Fujiki",
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T1 - Synthetic analogues (indolactams) of (-)-indolactam-V are new congeners of the teleocidin class of tumor promoters

AU - Hirota, Mitsuru

AU - Suganuma, Masami

AU - Yoshizawa, Shigeru

AU - Horiuchi, Takahiko

AU - Nakayasu, Michie

AU - Hasegawa, Masashi

AU - Endo, Yasuyuki

AU - Shudo, Koichi

AU - Fujiki, Hirota

PY - 1987/6/1

Y1 - 1987/6/1

N2 - (-)-Indolactam-V, which has the partial structure of teleocidins A and B, and has tumor-promoting activity, is a good model for use in studies on the relation between structure and tumor-promoting activity, whereas (+)-indolactam-V has no tumor-promoting activity. In this work, five racemic indolactams differing only in their alkyl group at C-12 of (-)-indolactam-V were synthesized and tested for biological and biochemical activities related to tumor promotion. The activities tested were inductions of ornithine decarboxylase in mouse skin and human promyelocytic leukemia (HL-60) cell adhesion, inhibition of specific [3H]12-O-tetradecanoyl-phorbol-13-acetate binding to a mouse particulate fraction and activation of protein kinase C in vitro. The results showed that (±)-indolactam-L and (±)-indolactam-F had almost the same activities as (±)-indolactam-V, suggesting that (-)-indolactam-L and (-)-indolactam-F are new tumor promoters with as high potency as (-)-indolactam-V. (±)-Indolactam-t-L, which has a highly lipophilic group at C-12 of (-)-indolactam-V, showed the highest activities in the above tests. (-)-Indolactam-t-L might have stronger tumor-promoting activity than (-)-indolactam-V. Furthermore, the results with (-)-indolactam-t-L indicated the possibility of designing new tumor promoters with stronger activity than teleocidin.

AB - (-)-Indolactam-V, which has the partial structure of teleocidins A and B, and has tumor-promoting activity, is a good model for use in studies on the relation between structure and tumor-promoting activity, whereas (+)-indolactam-V has no tumor-promoting activity. In this work, five racemic indolactams differing only in their alkyl group at C-12 of (-)-indolactam-V were synthesized and tested for biological and biochemical activities related to tumor promotion. The activities tested were inductions of ornithine decarboxylase in mouse skin and human promyelocytic leukemia (HL-60) cell adhesion, inhibition of specific [3H]12-O-tetradecanoyl-phorbol-13-acetate binding to a mouse particulate fraction and activation of protein kinase C in vitro. The results showed that (±)-indolactam-L and (±)-indolactam-F had almost the same activities as (±)-indolactam-V, suggesting that (-)-indolactam-L and (-)-indolactam-F are new tumor promoters with as high potency as (-)-indolactam-V. (±)-Indolactam-t-L, which has a highly lipophilic group at C-12 of (-)-indolactam-V, showed the highest activities in the above tests. (-)-Indolactam-t-L might have stronger tumor-promoting activity than (-)-indolactam-V. Furthermore, the results with (-)-indolactam-t-L indicated the possibility of designing new tumor promoters with stronger activity than teleocidin.

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